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Cavallari Holiday Rentals

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Cavallari holiday rentals

A stone building with a courtyard, a swimming pool, and vineyard fields in the background.

1. Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (42 reviews)
"Great place to stay in Tuscany! Very nice breakfast also!"
United States
Janet
The price is NZ$387
includes taxes & fees
19 Oct - 20 Oct
Riserva di Fizzano Residence
A restaurant with hanging baskets of greenery, wicker furniture, and a view of the outdoors.

2. Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (80 reviews)
"Amazing property and room, only issue is it’s very understaffed so it’s hard to get anything without chasing down workers. They also don’t stay on the property so after like 11pm you’re on your own. Besides that it was a wonderful location and very peaceful."
United States
Gage
The price is NZ$555
includes taxes & fees
16 Oct - 17 Oct
Terre di Baccio
A balcony with a table, chairs, and a bottle of wine, overlooking a vineyard and distant hills.

3. Casa Vacanze Squarcialupi

Casa Vacanze Squarcialupi
Castellina in Chianti
9.2 out of 10, Wonderful, (5 reviews)
"Staff was very helpful. Was a bit bummed the pool was closed as that was part of the reason for choosing the hotel. "
United States
Jeffrey
The price is NZ$236
includes taxes & fees
6 Nov - 7 Nov
Casa Vacanze Squarcialupi
A balcony with a view of rolling hills, a table with a book and a bottle, and a chair.

4. Villa San Filippo

Villa San Filippo
4.0 star property
Barberino Val d'Elsa
8.6 out of 10, Excellent, (56 reviews)
"This place was beautiful, quiet like a picture you’d see in the movies"
Canada
Nadia
The price is NZ$191
includes taxes & fees
21 Oct - 22 Oct
Villa San Filippo
A stone building with a garden in front.

5. Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 10, Exceptional, (28 reviews)
"What an amazing place. We enjoyed it so much."
United States
Tatevik
The price is NZ$351
includes taxes & fees
15 Oct - 16 Oct
Borgo Argenina
A table with breakfast items and a view of rolling hills.

6. Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Tavarnelle Val di Pesa
8.6 out of 10, Excellent, (121 reviews)
"It’s seen its best day a while ago. Basic necessities for an overnight, but I wouldn’t choose it again."
United States
Winonah
The price is NZ$163
includes taxes & fees
10 Oct - 11 Oct
Chianti Village Morrocco
A pool area with lounge chairs and umbrellas, surrounded by greenery and a stone building.

7. Residenzia del Sogno

Residenzia del Sogno
Castellina in Chianti
9.6 out of 10, Exceptional, (15 reviews)
"Beautiful and authentic place, lovely couple running the place that care about you and your stay. "
Canada
Katherine
The price is NZ$268
includes taxes & fees
10 Oct - 11 Oct
Residenzia del Sogno
A kitchen with wooden cabinets, a glass display case, and a dining area with a table and chairs.

8. Mariani Bed & Breakfast

Mariani Bed & Breakfast
Castellina in Chianti
9.8 out of 10, Exceptional, (18 reviews)
"Beautiful view, very clean and everything in great condition. Friendly service. We will definitely stay again."
United States
Frank
The price is NZ$174
includes taxes & fees
14 Oct - 15 Oct
Mariani Bed & Breakfast
A dining area with a wooden table, a chair, and a sofa. There is a window with pink curtains, a vase with flowers, and two wine glasses on the table.

9. Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.8 out of 10, Exceptional, (102 reviews)
"We love this beautiful exquisitely appointed hotel in a town with unexpected treasures and great food "
United Kingdom
John
The price is NZ$231
includes taxes & fees
8 Nov - 9 Nov
Palazzo Pacini
A dining area with a table set for two, featuring a view of greenery through a window.

10. La Locanda di Pietracupa

La Locanda di Pietracupa
Tavarnelle Val di Pesa
9.6 out of 10, Exceptional, (39 reviews)
"Great place, wonderful restaurant"
Germany
Isabell
The price is NZ$262
includes taxes & fees
7 Nov - 8 Nov
La Locanda di Pietracupa
A stone building with multiple windows and a chimney.

11. Agriturismo La Ferrozzola

Agriturismo La Ferrozzola
Castellina in Chianti
9.4 out of 10, Exceptional, (9 reviews)
"Very nice agriturismo. "
United States
Ruth
The price is NZ$260
includes taxes & fees
8 Nov - 9 Nov
Agriturismo La Ferrozzola
A rectangular swimming pool with a clear blue water surface, surrounded by a brick patio. There are several lounge chairs and umbrellas around the pool area.

12. Villa Rosa Panzano

Villa Rosa Panzano
Greve in Chianti
8.2 out of 10, Very good, (57 reviews)
"A lovely rural B&B with very kind staff."
Canada
Allison
The price is NZ$272
includes taxes & fees
11 Oct - 12 Oct
Villa Rosa Panzano
A stone building with a yellow sign reading "b&b erioico".

13. L' Eroico

L' Eroico
Gaiole in Chianti
10.0 out of 10, Exceptional, (15 reviews)
"Monica is a very gracious host. We very much enjoyed our stay. The village is also very quaint and within walking distance. We appreciate the hospitality and highly recommend staying here if you’re coming to the area."
United States
Angela
The price is NZ$283
includes taxes & fees
2 Nov - 3 Nov
L' Eroico
A villa with a swimming pool, outdoor seating, and a tennis court.

14. Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (80 reviews)
"Beautiful resort in the hills, lovely and charming room, incredibly spacious."
United States
Deanna
The price is NZ$220
includes taxes & fees
19 Oct - 20 Oct
Villa Curina Resort
A pool area with two rectangular pools, surrounded by lounge chairs and umbrellas, set against a backdrop of vineyards and tall cypress trees.

15. Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (40 reviews)
"Great spot"
Canada
Philippe
The price is NZ$329
includes taxes & fees
12 Oct - 13 Oct
Villa di Sotto
An aerial view of a hotel with a swimming pool, outdoor seating area, and well-maintained gardens.

16. Antica Pieve B&B

Antica Pieve B&B
Tavarnelle Val di Pesa
9.4 out of 10, Exceptional, (15 reviews)
"Very nice stay here! Great breakfast and coffee every morning. Great location to tour around to different wineries and towns. Free parking. "
Canada
Jessica
The price is NZ$298
includes taxes & fees
11 Oct - 12 Oct
Antica Pieve B&B
An outdoor swimming pool with a wooden pergola, lounge chairs, and a stone wall backdrop.

17. Guild Living Siena Senior Resort & Residence

Guild Living Siena Senior Resort & Residence
Scacciapensieri
8.8 out of 10, Excellent, (55 reviews)
"Amazing! Thank you!"
United Kingdom
Lucy
The price is NZ$260
includes taxes & fees
3 Nov - 4 Nov
Guild Living Siena Senior Resort & Residence
A rustic stone building with a courtyard.

18. Fullino Nero

Fullino Nero
Siena
9.6 out of 10, Exceptional, (56 reviews)
"Great stay! Clean rooms with air conditioning. Beautiful grounds "
United States
Christian
The price is NZ$217
includes taxes & fees
11 Oct - 12 Oct
Fullino Nero
An arched brick corridor with gravel flooring, potted plants, and a gate leading to a garden area.

19. Ca' Bianca Tuscany Relais

Ca' Bianca Tuscany Relais
Siena
10.0 out of 10, Exceptional, (46 reviews)
"Clean room, amazing staff"
Canada
Talha
The price is NZ$480
includes taxes & fees
12 Oct - 13 Oct
Ca' Bianca Tuscany Relais
A bedroom with a bed, a bedside table, a TV mounted on the wall, and a sliding glass door leading to a balcony with a view of greenery and hills.

20. Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.2 out of 10, Wonderful, (31 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is NZ$148
includes taxes & fees
2 Nov - 3 Nov
Tuscasì Aparthotel
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Cavallari Hotel Reviews

Hotel Athena

Hotel Athena

10/10 Excellent
"Lovely hotel in Siena. Well located for exploring on foot with the main Palazzo and the Duomo no more than 15 minutes away. Really enjoyed the rooftop patio!"
Hillaine 3-night trip
Posted 10 hours ago
Hotel Athena

Find out more about Cavallari

Everything you need to know about Cavallari holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Cavallari holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Cavallari holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Cavallari holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cavallari. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Cavallari holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Cavallari holiday rentals we have selected for you start as low as NZ$88 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Cavallari rentals

At Expedia, we put the best Cavallari holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Cavallari rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Cavallari holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Cavallari. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Cavallari?

Yes, there are holiday rentals close to the most popular sights in Cavallari, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Cavallari has to offer?

Borgo Argiano: This holiday home rental outside of Cavallari is located on a river, and has a balcony, a terrace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and kitchenware. You can relax into your holiday with a garden and a library.

How many holiday rentals will I find in Cavallari?

Choose from 3 Expedia holiday rentals in Cavallari for a memorable holiday.

What’s there to see and do in Cavallari?

While exploring the area, visit family-friendly sights like Borgo di Vescine - Tenute di Castelvecchi, or get outside and enjoy nature at Arno River. In the wider area, you’ll find City Hall Castellina In Chianti and Il Molino di Grace Winery.

What’s a holiday rental in Cavallari like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Cavallari. Holiday rentals offer extras such as hot tubs, fire pits and patios so you'll be comfy for your stay. If you're concerned about a sanitised environment, holiday rentals can provide a sense of privacy away from public hotel lifts and busy front desks while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive choice for families.